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Naphthalene

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Reaction thermochemistry data

Go To: Top, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C10H7- + Hydrogen cation = Naphthalene

By formula: C10H7- + H+ = C10H8

Quantity Value Units Method Reference Comment
Deltar394.2 ± 1.2kcal/molBranReed and Kass, 2000gas phase; B
Deltar394.2 ± 1.2kcal/molTDEqMeot-ner, Liebman, et al., 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Deltar394.0 ± 5.0kcal/molCIDCLardin, Squires, et al., 2001gas phase; B
Quantity Value Units Method Reference Comment
Deltar385.6 ± 1.3kcal/molH-TSReed and Kass, 2000gas phase; B
Deltar383.8 ± 1.2kcal/molTDEqMeot-ner, Liebman, et al., 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Deltar385.4 ± 5.1kcal/molH-TSLardin, Squires, et al., 2001gas phase; B

C6H7N+ + Naphthalene = (C6H7N+ bullet Naphthalene)

By formula: C6H7N+ + C10H8 = (C6H7N+ bullet C10H8)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar15.4kcal/molPHPMSEl-Shall and Meot-Ner (Mautner), 1987gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar26.cal/mol*KN/AEl-Shall and Meot-Ner (Mautner), 1987gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
7.3324.PHPMSEl-Shall and Meot-Ner (Mautner), 1987gas phase; Entropy change calculated or estimated; M

C12H8+ + Naphthalene = (C12H8+ bullet Naphthalene)

By formula: C12H8+ + C10H8 = (C12H8+ bullet C10H8)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar12.6kcal/molPHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar28.cal/mol*KN/AMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar5.1kcal/molPHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M

C12H9+ + Naphthalene = (C12H9+ bullet Naphthalene)

By formula: C12H9+ + C10H8 = (C12H9+ bullet C10H8)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar13.9kcal/molPHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar28.cal/mol*KN/AMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar6.4kcal/molPHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M

2Hydrogen + Naphthalene = Naphthalene, 1,2,3,4-tetrahydro-

By formula: 2H2 + C10H8 = C10H12

Quantity Value Units Method Reference Comment
Deltar-29.8kcal/molEqkFrye and Weitkamp, 1969gas phase; ALS
Deltar-28.8 ± 1.2kcal/molEqkWilson, Caflisch, et al., 1958gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -32.0 ± 1.2 kcal/mol; At 400 K; ALS

Benzobicyclo[2.2.0]hexa-2,5-diene = Naphthalene

By formula: C10H8 = C10H8

Quantity Value Units Method Reference Comment
Deltar-59.4 ± 1.9kcal/molEqkDreeskamp, Kapahnke, et al., 1988liquid phase; solvent: Heptane; Isomerization; ALS
Deltar-59.6 ± 1.9kcal/molCisoGrimme and Heinze, 1978liquid phase; solvent: Heptane; ALS

C10H8+ + Naphthalene = (C10H8+ bullet Naphthalene)

By formula: C10H8+ + C10H8 = (C10H8+ bullet C10H8)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar17.8kcal/molPHPMSMeot-Ner (Mautner), 1980gas phase; M
Quantity Value Units Method Reference Comment
Deltar29.cal/mol*KPHPMSMeot-Ner (Mautner), 1980gas phase; M

C10H7- + Hydrogen cation = Naphthalene

By formula: C10H7- + H+ = C10H8

Quantity Value Units Method Reference Comment
Deltar395.5 ± 1.3kcal/molBranReed and Kass, 2000gas phase; B
Quantity Value Units Method Reference Comment
Deltar386.9 ± 1.4kcal/molH-TSReed and Kass, 2000gas phase; B

H4O4- + Naphthalene + 2Water = C10H12O4-

By formula: H4O4- + C10H8 + 2H2O = C10H12O4-

Quantity Value Units Method Reference Comment
Deltar52.3 ± 2.3kcal/molN/ALe Barbu, Schiedt, et al., 2002gas phase; Affinity is difference in EAs of lesser solvated species; B

H2O3- + Naphthalene + Water = C10H10O3-

By formula: H2O3- + C10H8 + H2O = C10H10O3-

Quantity Value Units Method Reference Comment
Deltar37.8 ± 2.3kcal/molN/ALe Barbu, Schiedt, et al., 2002gas phase; Affinity is difference in EAs of lesser solvated species; B

C10H9+ + Naphthalene = (C10H9+ bullet Naphthalene)

By formula: C10H9+ + C10H8 = (C10H9+ bullet C10H8)

Quantity Value Units Method Reference Comment
Deltar14.1kcal/molPHPMSMeot-Ner (Mautner), 1980gas phase; M
Quantity Value Units Method Reference Comment
Deltar30.cal/mol*KPHPMSMeot-Ner (Mautner), 1980gas phase; M

Oxygen anion + Naphthalene = C10H8O2-

By formula: O2- + C10H8 = C10H8O2-

Quantity Value Units Method Reference Comment
Deltar22.1 ± 2.3kcal/molN/ALe Barbu, Schiedt, et al., 2002gas phase; Affinity is difference in EAs of lesser solvated species; B

Nitric oxide anion + Naphthalene = C10H8NO-

By formula: NO- + C10H8 = C10H8NO-

Quantity Value Units Method Reference Comment
Deltar14.5 ± 2.3kcal/molN/ALe Barbu, Schiedt, et al., 2002gas phase; Affinity is difference in EAs of lesser solvated species; B

C10H8NO- + 2Naphthalene = C20H16NO-

By formula: C10H8NO- + 2C10H8 = C20H16NO-

Quantity Value Units Method Reference Comment
Deltar23.8 ± 2.3kcal/molN/ALe Barbu, Schiedt, et al., 2002gas phase; Affinity is difference in EAs of lesser solvated species; B

5Hydrogen + Naphthalene = Naphthalene, decahydro-, cis-

By formula: 5H2 + C10H8 = C10H18

Quantity Value Units Method Reference Comment
Deltar-76.0kcal/molEqkFrye and Weitkamp, 1969gas phase; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Reed and Kass, 2000
Reed, D.R.; Kass, S.R., Experimental determination of the alpha and beta C-H bond dissociation energies in naphthalene, J. Mass Spectrom., 2000, 35, 4, 534-539, https://doi.org/10.1002/(SICI)1096-9888(200004)35:4<534::AID-JMS964>3.0.CO;2-T . [all data]

Meot-ner, Liebman, et al., 1988
Meot-ner, M.; Liebman, J.F.; Kafafi, S.A., Ionic Probes of Aromaticity in Annelated Rings, J. Am. Chem. Soc., 1988, 110, 18, 5937, https://doi.org/10.1021/ja00226a001 . [all data]

Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B., Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine, J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z . [all data]

Lardin, Squires, et al., 2001
Lardin, H.A.; Squires, R.R.; Wenthold, P.G., Determination of the electron affinities of alpha- and beta- naphthyl radicals using the kinetic method with full entropy analysis. The C-H bond dissociation energies of naphthalene, J. Mass Spectrom., 2001, 36, 6, 607-615, https://doi.org/10.1002/jms.159 . [all data]

El-Shall and Meot-Ner (Mautner), 1987
El-Shall, M.S.; Meot-Ner (Mautner), M., Ionic Charge Transfer Complexes. 3. Delocalised pi Systems as Electron Acceptors and Donors, J. Phys. Chem., 1987, 91, 5, 1088, https://doi.org/10.1021/j100289a017 . [all data]

Meot-Ner (Mautner), 1980
Meot-Ner (Mautner), M., Dimer Cations of Polycyclic Aromatics: Experimental Bonding Energies and Resonance Stabilization, J. Phys. Chem., 1980, 84, 21, 2724, https://doi.org/10.1021/j100458a012 . [all data]

Frye and Weitkamp, 1969
Frye, C.G.; Weitkamp, A.W., Equilibrium hydrogenations of multi-ring aromatics, J. Chem. Eng. Data, 1969, 14, 372-376. [all data]

Wilson, Caflisch, et al., 1958
Wilson, T.P.; Caflisch, E.G.; Hurley, G.F., The naphthalene-tetralin-hydrogen equilibrium at elevated temperature and pressure, J. Phys. Chem., 1958, 62, 1059. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Dreeskamp, Kapahnke, et al., 1988
Dreeskamp, H.; Kapahnke, P.; Tochtermann, W., Photo valence isomerization of sterically strained aromatic hydrocarbons: 8,9-dicarbethoxy[6]paracyclophane, Radiat. Phys. Chem., 1988, 32, 537-539. [all data]

Grimme and Heinze, 1978
Grimme, W.; Heinze, U., Kinetics and enthalpy of isomerization of benzobicyclo[2.2.0]hexa-2,5-diene, Chem. Ber., 1978, 111, 2563-2570. [all data]

Le Barbu, Schiedt, et al., 2002
Le Barbu, K.; Schiedt, J.; Weinkauf, R.; Schlag, E.W.; Nilles, J.M.; Xu, S.J.; Thomas, O.C.; Bowen, K.H., Microsolvation of small anions by aromatic molecules: An exploratory study, J. Chem. Phys., 2002, 116, 22, 9663-9671, https://doi.org/10.1063/1.1475750 . [all data]


Notes

Go To: Top, Reaction thermochemistry data, References